4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid → HCID 70656839, compound

HRID 872623Notes

Reaction equation

HRID 872623 reaction equation
[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[C:3]([C:10]([OH:12])=O)[CH:2]=1.[NH2:13][C@@H:14]([CH3:30])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=2)=[N:17]1>>[Cl:29][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:10]([C:3]3[CH:2]=[N:1][N:5]4[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=34)=[O:12])[CH3:30])[N:17]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

3

Reactant 2

HCID 219413764,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656839HCID 70656839, compoundYield 55.5%

Procedure

The title compound was prepared as described in Example 34(d), starting from 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid (0.127 g, 0.767 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.2 g, 0.767 mmol). The product was purified by flash-chromatography. Yield 55.5%. 1H-NMR (400 MHz; DMSO-d6): δ 1.12 (d, 3H), 1.66-1.75 (m, 2H), 1.85-1.95 (m, 2H), 2.87 (t, 2H), 4.02 (t, 2H), 4.22-4.23 (m, 2H), 4.32-4.42 (m, 1H), 6.94 (d, 1H), 7.72 (d, 1H), 7.80 (d, 1H), 7.83 (s, 1H), 7.91 (dd, 1H), 7.97 (d, 1H), 8.06 (d,

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-5c971d28cc7741dc86b5c88f8b3c63cc
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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